I've always had a hard time getting into history because in my head, I'm studying statues and oil paintings and not human beings. A few years ago I was doing some reading up on the American Revolution and it was all just a bunch of names of key players, but I had a hard time getting invested in the people, or emphasizing with them as people for that matter. It is hard for me to understand who is who, who is allegiant to whom, etc. They are just names to me.
I recently started getting into the Hamilton soundtrack and that has resparked my interest in the era and the events leading up to the war and its aftermath. Now I can read about all these principles like John Laurens, Lafayette, Burr, etc., and have a human backstory that provides context. This makes it so much easier to dig deeper into reading. It puts a human spirit to the name - which I have a hard time doing just reading text books.
My question is, absent an award-winning Broadway musical or good movie on a historic subject, how do I get to the same level of empathy for historic events or people that I get when it is presented in a medium that I really enjoy, such as the Hamilton musical? How do I read text books and find the "story" that interests me to dig deeper?
Textbooks don't really give you the thing you are really looking for because the purpose of a textbook is to give you some narrative overview, a timeline, etc. All of these are essentially the starting points. What I would suggest that you need to do is to mine the footnotes and find primary sources associated with the bit that you are reading. You may well find that the primary sources still don't quite hit the same spot as the amazing Hamilton. A lot of primary sources are, honestly, dull in places or are tricky to read because of differences in language and style. But there is joy in the mundane. Finding that is something that takes a bit of practice too. Finally, too much empathy can be quite tough on the individual. Some of the primary sources record such tragic or unpleasant things that it is quite burdensome.
As a starting point, do a wee bit of googling around the key players, chase down primary sources and then read bits of them asking lots of questions about the content and how you might understand/relate to this person if they were standing in front of you today. I hope you find some things that help bring history to life for you.
Documentaries and movies usually help me, as they, just like the musical, depict once distant historical figures as emotional, animated and alive. Perhaps reading a biography about a figure who's peaked your interest may allow you to delve into said person's life beyond just some dates (depending on how well the book is written, of course). If you want to know more about the 'people' (i.e. not singular figures), reading social-history books with interwoven contemporary sources can really bring out the climate and general atmosphere of the time period (for example, (bare in mind I haven't read it) Orlando Fige's The Whisperers uses letters, memoirs and conversations throughout to describe the Russian people's lives under Stalin). Hope this helps.